---
title: "The Hidden Problem Killing Workplace Culture"
episode: 70
podcast: "The LeanScale Podcast"
publisher: "LeanScale"
guest: "Tom Witte"
guest_title: "Chief Revenue Officer, Upflex"
date_published: 2026-05-15
date_modified: 2026-07-22
duration: 00:53:22
word_count: 8036
topics: ["sales-leadership", "ai-in-gtm", "sales-enablement", "revenue-operations"]
canonical_url: https://leanscale-knowledge-hub.netlify.app/podcast/tom-witte-workplace-culture/
source: "LeanScale Podcast Knowledge Hub — https://leanscale-knowledge-hub.netlify.app"
license: "Free to quote and cite with attribution to The LeanScale Podcast."
---

# The Hidden Problem Killing Workplace Culture — Full Transcript

> Episode 70 of The LeanScale Podcast, with Tom Witte.
> Published May 15, 2026 · 00:53:22 · 8,036 words.
> Machine-transcribed and **not diarized** — speaker attribution is inferred, so verify
> attribution against the audio before quoting a specific person.
> Structured breakdown: https://leanscale-knowledge-hub.netlify.app/podcast/tom-witte-workplace-culture/

## 00:00 — Meet Tom Witte: 15 years making work better

**[0:00]** Today, I'm talking with Tom Whitty, CRO at UpFlex. Tom has spent the last 15 years in employee experience from benefits to well-being to workplace, helping companies think about what actually enables people to do their best work. He's built through crises, including starting a wealth management business just prior to the '08 financial crash. And today, he brings that operator mindset to one of the biggest questions leaders are wrestling with. How do you create flexibility, connection, and performance all at the same time? We'll also talk about what it means to be an AI-first revenue leader and how Tom thinks about building

**[0:42]** teams and systems that work in the real world. Tom, you spent 15 years across benefits, well-being, and now workplace, which is a very hot topic. What is the through-line? What problem do you feel you have actually been trying to solve all along? Yeah, thanks, Anthony, and great question. I think for me, first off, I've always been someone that needs to be really motivated by the mission regardless of what I'm doing. And for me, a mission that's been, I guess, really the through-line through all this work in my post-financial days has really been under the banner of making work better in some way,

**[1:23]** shape, or form. And that has taken different forms, as you mentioned, working in benefits and well-being, employee experience platforms, now more recently in workplace and workspace, optimization. But the idea that we spend half, if not more, of our waking hours at work and devote so much of our lives to it, if there's anything that I think is worthy of the effort to try and improve its work in way, shape, or form. It may also have been sparked by maybe one of my favorite movies from the '90s office space and us wanting to see if we could shift the needle away from that being the standard of corporate America.

## 02:09 — Where leaders get remote vs. return-to-office wrong

**[2:09]** That's a classic. I've definitely felt myself wanting to just destroy a printer every now and then. I've never had one that works. It's like printers and ice machines. No, never, never, never. I'm not sure how we have the most powerful AI in the history of the world, but we can't figure out those two things. Exactly. No, I think it's a very, very worthy pursuit. And you're right. We spend so much time in this boat of life. And I'm wondering, what do you think a lot of leaders are getting wrong with their approach, especially with the conversation around remote work or return to office?

**[2:50]** It's tough. I mean, it really depends on the company. I guess I'm somewhat disappointed in how much of a binary conversation it's become, right? And that our organization is either in office or remote/flexible. And the way of evolving how and where we work has been, I guess, behind what I would have maybe anticipated or expected. Some companies, of course, have certain motivations for trying to force folks back into their own corporate locations. Maybe they've made investments into those locations they want to see a lively environment when they walk around. Maybe it's a control issue. And I

**[3:41]** can't really trust that our people are working if I can't see that they're working directly in front of me. Maybe it's antiquated notions around, this is the only possible way that connection and culture can form, is if everyone is forced together in this one particular space, four or five days a week. It's really a bit of a hodgepodge, I think, of motivations. But I think the wrong part that's maybe a bit of a common denominator is we've really failed to, I think, adopt the way of thinking that different teams, different peoples, different organizations are going to do their best work differently. And I think the one common denominator

## 04:27 — LeanScale's remote journey and the have/have-nots problem

**[4:27]** also, another common denominator, is that we don't necessarily have to be co-located in the same space all the time to get the benefit and sort of wring the juice out of connection, collaboration, and culture. And there needs to be some of that for sure, and we can be intentional about that. It just doesn't have to be all the time. Yeah, and I think I've had my own experience with this at LeanScale. We started in 2021, so right after pandemic times. My co-founder is in Brazil, so we had to start remote, unless I want to move to Brazil or him up here. And I found at the very early stage, I really,

**[5:14]** really enjoyed actually being in office. And I had a core team, I'm based in Phoenix, and we had the core team out here in Phoenix where we could get things started and communication flowed really well. And then when we got to a certain point where we had people in different areas all around the world, it started to become a have and have nots issue, where I was present in the office, so people around me had more access to me than people who are remote. And we made the decision to go fully remote, even though a lot of us live nearby each other, simply to even the playing field and have everybody in the same rhythm.

**[5:54]** Yeah, I don't know. Like I said, to me, it's not a binary, right? I think that people being isolated in their homes, you know, five days a week is just as wrong, you know, for lack of a better term than people being forced to spend 40 hours a week in the office, right? Where we know, almost guaranteed, they're gonna be spending a good chunk of that time on Zoom meetings or Teams meetings with other folks distributed somewhere else in the world, right? You know, the distributed way of working has taken such root across most organizations at this point, especially when they hit a certain point in the scale, that it's gonna

**[6:35]** be, that's just gonna be the nature of things. And so, but again, being home, you know, locked away in your room, that's not great either, right? But there's a balance and there's I think a way of ensuring that those human connections, those moments that matter, that magic X factor, which is undeniable, right? Like no one's saying that this doesn't exist, that comes to fruition when folks spend time together with the, you know, in person. That can still happen. That can still be harvested and engineered even to a large degree by just being intentional and how, you know, how you bring folks together. I'm just of the opinion personally, that we

## 07:17 — What makes an office worth showing up for

**[7:17]** don't need to, you know, hope that it happens by chance and luck by forcing everyone into the same space all the time. Yeah, I think there is an intentionality behind how you design this. On the office side, in your opinion, what makes an office worth showing up for? That's a great question. Something we think a lot about and especially in my current line of work here at my company, UpFlex, where, you know, now I've again sort of moved, I'm in the workspace phase of my employee experience journey, if you will. And because again, I'm certainly not anti-office and I think that, you know, that there's a lot that comes from,

**[8:04]** you know, having that great office environment. But for me, it goes back to the old saying, "It's not what you're doing. It's who you're doing it with." Although I might adapt that old phrase a little bit to say it's not sort of the building that you're doing it in. It's who you're doing it with, right? Because so many times companies have really focused on the space itself to be that magnet or to be that draw. We want to have the best office possible with all the amenities and all the right types of workspaces and the niceties that will make being there great. And don't get me wrong,

**[8:46]** that stuff is important. It's helpful. It does enrich the experience for sure. But on the other side is this much bigger piece of the pie, which is it's the interactions with people that I'm going to have there that either makes it a fulfilling worthwhile experience, something I couldn't have gotten from home, right? If I'm not working with Anthony on something and I don't then get to spend time with Anthony, like shoulder to shoulder working on that thing, whatever it might be together, right? In that really kind of X factor of magic way, that's the thing, right? And so I would argue that we've, we've sort of overlooked

## 09:36 — Orchestration beats amenities (the dumpster-fire office)

**[9:36]** that piece of the pie a bit in really what I tend to speak about is, you know, the concept of orchestrating folks in this hybrid world that we live in, you know, how we orchestrate folks day to day within space is actually the much more powerful magnet than, you know, how nice the space is itself. I'll share the first lean scale office was an absolute dumpster fire. Yeah. I'm pretty sure nobody maintained the building. There was a constant smell of sewage throughout the entire building, inches of dust around everything, but it was dirt cheap. And everybody that we cared about working with was there. And I will tell you those moments were magical.

**[10:25]** We had an amazing time. Yes. And yeah, it didn't have anything fancy. We had a horrible Keurig machine in the corner of our room that we rented out of this space. And that was about it. Those are the amenities. So I think I, from my own experience, I agree. It's all about the people. If you're doing work that matters with the people that are in proximity, then that's where being in person can be really valuable. Really agree. And, you know, so where we read a rigid for like, for a long time, I tried to come at that, that problem by working with companies on playbook strategies for intentional

**[11:07]** connections. And we worked with all sorts of workplace and culture and IO psychologist type experts, um, to help really companies help companies really think about how to win. We asked folks to come together. How do we make sure when they show up, it's that kind of intentional experience, right? It's not just haphazard, but they're not going to show up and sit on zooms, right? But there's a reason why they're there. The right people are there for that particular reason. Um, and they can have that kind of experience, which may only need to be every so often or these days a week, or obviously every team

**[11:43]** company is different. Um, what we still found though, is even when we had that playbook, it was really, really hard for companies to implement that into practice. Um, using traditional approaches to occupancy planning or, you know, organizing team, you know, adjacencies and calendars and which, you know, which teams, people, et cetera, came in on which days and where were they sat? It was a really, really hard problem, um, to solve even pre COVID and then became an exponentially harder problem to solve post COVID when hybrid became the mainstay model. And now you had hybrid variability and choice introduced at the person and team

## 12:30 — The orchestration Rubik's cube AI can finally solve

**[12:30]** level in terms of largely where and when they would be. And so that orchestration problem, that Rubik's queue problem of orchestrating people on a day-to-day basis that honored their requirements, team connections and adjacencies and the work that they were actually doing at any given point with one another, that quickly exceeded the capabilities of humans. And that's where I think, you know, we've really latched onto AI as being really sort of like what AI is best at, um, to help solve that problem for companies on a day-to-day basis. And so that's really where we spend the majority of our focus these days is how

**[13:13]** can we leverage these types of modern tools to solve that Rubik's cube on a day-to-day basis to ensure that when folks do show up, it's that perfect experience and they didn't have to do anything like they didn't have to book and book a desk. They didn't have to indicate when they were coming in, right? That self-organization and friction that is associated with it is sort of gone and now we can just guide them to when and where with the right people to have those incredible experiences. So that's been a, I would say one of the certain upsides we've seen, you know, emerge out of AI.

## 13:48 — Warning signs and the Swiss cheese effect

**[13:48]** Absolutely. What, what potential warning signs start to show up in organizations when this org design really starts to demand your attention? It'll probably start to show up when, you know, the, usually the conditions we see are first the company has put the onus on employees to have to figure it out, right? We think we're doing a good job in giving you flexibility and degrees of choice, but then that just creates work and burden for me to now have to navigate that, to make those decisions and to coordinate those decisions en masse with my colleagues in the best possible way. And so there'll be some, I think natural friction

**[14:43]** that shows up in that type of motion, whether it's low adoption of booking systems, people not actually doing what they indicate that they'll do. You'll see it when you walk around those spaces. And we sometimes refer to it as like the Swiss cheese effect, where there's two or three people over here and two or three people over there and a lot of gaps in space in between. So you may have a bunch of people in your building, but it kind of the, the energy feels really low, right? It doesn't feel very vibrant. And you're like, what are we doing wrong? Right? Like the space, and that's oftentimes actually where company like

**[15:24]** you kind of get the company will get to a fork in the road. We're like, there's no one. It feels like there's no one here, right? And the energy feels dead. We need to get everyone back in five days a week now, right? This, this whole hybrid thing's not working for us, right? We're losing our culture, right? Because it walks around, it feels that way. When in reality, it's just, well, if we could just organize people better in that space, right? You probably have too much space statistically. And if we could just organize people and sort of densify it a bit and make sure that we were getting the right groups together each

## 15:56 — Advice for 50–1,000-person scaling companies

**[15:56]** day, that energy and vibrancy would come up pretty dramatically. And it would feel like a completely different experience for we work with a lot of companies that are maybe in a scaling phase. So they probably have anywhere from 50 to a thousand employees and everything in between, mostly B2B tech startups, some in AI, SAS. What recommendations would you give them? What, what have you seen to work well in that context that still helps foster that human connection, keep a through line of culture across the whole organization, but also gives the flexibility that people are looking for?

**[16:42]** I think it first starts with because, as I mentioned now, a couple of times, every company, every team is different. They're all going to work differently. A finance company versus a tech company versus a food and beverage manufacturer, right, are going to have different ways of working that need to be optimized. And then from there, it's very different even at a team level, right? The engineering team and the sales team probably have different needs or are going to be optimized in different ways in with regards to their workforce and workplace policies. And so you need to first be willing to sort of raise your hand in the

**[17:25]** air and say, I recognize that it's different, right, that there is variability in what's best, what structure and what policy and what accommodations are best for each different group, each different cohort. And if you're willing to do that and then willing to listen and work with those teams to understand, well, what's the best way for you all to work, right, and try and engineer around that to a degree, that's, I think, the best first step, right? And that may change and evolve as your company gets bigger and bigger and bigger, right? And like with your own example that you just gave, right, like everyone being together,

## 18:06 — How distributed work scales in stages

**[18:06]** and I think you said that there was the Phoenix, if I'm not mistaken, right, like when you were all there, this makes a lot of sense, right? We've got this hub that we come into, you know, regularly and we're all together and we're figuring stuff out. And then pretty quickly we have employees here, there, and sort of everywhere. And then the next stage after that, typically, is there starts to be these localized clusters of folks in different pockets around the country or world, right? And so there's going to be different strategies for making sure that those localized clusters spend good quality time together for, again,

**[18:44]** very intentional reasons, that we get the whole company together for different sets of reasons. And then on a day-to-day basis that we allow teams to organize and sort of work in the way that's uniquely right for them. So it takes a little bit of work to do that, right? But I think it's work that's certainly worth the effort because if you can get that right, I mean, all of the, you know, pick an outcome. It's going to be there, whether that's, you know, sort of retention and productivity, but just, you know, precursors to that would just be satisfaction and, you know, the level of collaboration that people feel that they have in space.

**[19:30]** It's been a very difficult puzzle for me to solve. And it's something we actually spend a lot of time in meetings talking about, testing different things. And, you know, from the beginning, we had that in-person time and then we went fully remote. Definitely felt like we lost some connection. So then we started doing whole company off-sites. So we would meet for a week once a quarter. That was manageable when it was a small team. Then as we got bigger to bring the entire company, every single quarter was just not reasonable. It's a lot. So then we started doing smaller local meetups with local teams. And I think something that

**[20:08]** you mentioned that I think is really important for people to understand that this requires a lot of effort. You have to be intentional and it's something that you'll continually need to adapt and work on. And I don't know if people really have that realization. I agree. I mean, either they do in there and it's, you know, there's someone that makes a decision that says, you know what? That's too much, right? Like it's too much to handle. And I guess that, you know, it just really depends on if you feel that, you know, the ability to hire anywhere, right? How important is that to you, right? The ability to give

## 20:48 — Time as the most valuable asset; reciprocal care

**[20:48]** people flexibility back in their lives, right? Or the ability to give them time back, which I would argue is the most valuable asset in the world. And, you know, to be with their family, not miss certain moments, etc. How important is that to you as a business, right? You may just say it's not, right? And we don't care. And, you know, we haven't -- there's enough talent in, you know, Springfield that we're going to be able to meet our talent needs and we feel strongly that work is work and, you know, you're paid and so your time is our time and that's it, right? And if that's you, that's fine, right? That's okay. But

**[21:31]** if you do value those other things and if there is a way to do it and that way is getting increasingly easier and easier with the advent of modern tools. >> What are some good technologies you've seen? Because I think I've seen some like virtual office platforms. I've seen other, you know, very, very well built out presentation and meeting platforms that are specifically for like off-sites. Is there anything that you say, hey, I've seen this, it's worked really well and people trying to build a culture remotely should use this? >> I'm not too much an expert in like the virtual collaboration space. I mean, we have,

**[22:16]** you know, messaging and Zoom and, you know, pick your platform kind of thing. I think all that's great. I think most companies have adopted, you know, sort of those basic things. I haven't seen honestly too much novel there. I think, again, where we tend to focus is what tools can we use and deploy to help make orchestrating folks inside space or in coming together that much easier? That, you know, shifts the burden off of the employee, makes the administrative aspects of it, you know, very, very easy, if not fully autonomous, which is, you know, kind of quickly where we're getting to. You know, AI nowadays is

**[23:00]** good enough that it can read various signals from across the enterprise. It can understand team connections, people connections, what space requirements those teams and people may need, who should be with whom, when, right? And then understand also a level of collaboration dynamics that transcends the org chart to really infer like that proper grouping of folks on a day-to-day basis within space, and then actually do that. It can actually then allocate. And so that is sort of, I think, the next frontier of things in saying we can now adopt this autonomous model that's constantly monitoring data from around the enterprise

**[23:52]** in a way that humans could never have done in real time and continuously to optimize for right people in the right place at the right time on a day-to-day inconsistent basis. Is there anything in the data that has surprised you about what can increase productivity or satisfaction when considering how people are working in space? Surprising. I mean, I guess maybe a lot of times when we look at the starting point that companies have when it was a very, when, you know, there was variability due to some hybrid level choices available, and how inefficient humans are at self-organizing. That was a bit surprising, right? Because,

**[24:55]** you know, in the line of our work and we first, you know, kind of see, well, what's your starting point here? It's just hard, right? You know, it's just very, very hard, especially with large companies, right, and very complex workflows and team interactions. Trying to get that right, like when you tell a group of folks, like, hey, figure it out, right, and here's like some basic things you can use to, you know, signal to each other or indicate what, you know, what you're going to do and whatnot. Like, it doesn't get the needle very far. Going back to this again, I just think it's a much more complex problem than people appreciate,

**[25:39]** and I think the data that you have access to that you're seeing shows that as well, and I think there needs to be more investment in getting this right, because when you do get it right, I've worked in some very vibrant cultures before the pandemic, post pandemic, and you can tell the difference of when people are intentional about facilitating that culture, and like you said, not putting the onus on the employee to do it themselves or to figure it out amongst themselves, but intentionally creating those opportunities to collaborate and connect, it shows up in the results too. Productivity, satisfaction, retention, recruitment,

**[26:24]** it just really greases everything to make everything smoother. So what you just said, you know, it reminds me of when I was in my well-being employee experience days, like, we used to talk a lot about reciprocal care, and this loop, if you will, where if the company really demonstrated care for the employee, and that was felt and it was tangible, the employees will reciprocate that care back into the business, probably with dividends, right, and one of the most profound ways I think that employees can feel cared for is with respect to their time, right, and the type of life that you allow them to

**[27:06]** live, and that's where they'll fight, right, they will put themselves back into that job, they will fight for your business, they will go the extra mile, they will stay, they will work to keep that job even for lower compensation, statistically speaking, right, because that's how much they value these things, overwhelmingly. And so if you kind of get into that mindset of like, yeah, like, it's work, but that care is going to come back to us, and then some, that's where, you know, companies really get excited about, well, how do we figure it out? Yeah, and it's probably one of the most important problems for your company to solve. Agree, 100%. Yeah.

## 27:58 — Being an AI-first CRO: better, faster, cheaper

**[27:58]** We've talked a lot about how AI is being leveraged to make more intentional collaboration connection in space. I would love to hear as a CRO, how you're leveraging AI for your own go to market. Sure. So we're a really small team. We're really lean and scrappy, right? And unfortunately, you know, the team's gotten leaner over recent years. And the opportunity for us was to say, how can we offshore work that was really time consuming, that wasn't things that we could uniquely as humans do with respect to interacting with people in a sales pursuit or our customer relations, whatnot. How can we get more of that time back for ourselves? And that's where

**[28:57]** it started with us on our journey for, you know, adopting tools and really embedding them into our workflows. It's not like everyone here just has access to an LLM that they can use for, you know, whatever they want, although they can. But that wasn't the main thing. It was here's a process that we have as a business that sucks, right, that we hate doing, right? That is really problematic for whatever reason, right? Can we get AI to do this for us, right? Or can we use it to complete that process or task better, faster, cheaper, right? And we started to really adopt that mindset to basically everything that we do, right?

**[29:44]** And I still do it to this day whenever I find myself, catch myself going to do something, I ask myself, can I do this better, faster, cheaper through the use of, you know, our AI tools? Oftentimes the answer is yes, right? And if we prove that out, then we then say, all right, well, this is the way as a company that we're going to operate with respect to doing X, right? And so we had to really take a leap of and the upfront work of connecting these tools into our whole data ecosystem, right? Because it can only do certain things if you give it obviously the access to the requisite data and information it needs to

**[30:27]** perform that task. But once we had sort of the pipes connected and integrated with not only our data sources, but the tools that we, you know, used for different work functions like email, calendaring, et cetera, then we found that we could really increase the output of folks pretty dramatically or the time spent on non-revenue producing activities pretty dramatically by offshoring that work to AI. And even just over the last couple of months as models continuously get better and better and better, those outputs are just getting, you know, that much better. And so even the time that we used to have to spend saying,

**[31:12]** all right, the initial output from the AI model is going to be our V1 that's maybe 75, 80% of the way there. And now we're just going to spend the remaining time, you know, finishing that last 25% or so. Now, you know, the initial V1 outputs are coming out like 95% good, right? And that's just over the last few months. And so it's insane to think about where we'll be in, you know, just another few months or gosh, even a few years where you have to believe that there'll be just, you know, purpose-built agent armies like just ready to deploy and, you know, for different team functions and whatnot. And that seems to be where we're

**[31:54]** headed. And so we're trying to stay ahead of the curve and become the skilled operators of these kinds of agents and tools as we can and figure out how to maximize ourselves, especially knowing that, you know, we're trying to still grow revenue at no less of a rate, but with a good amount less resources. The last quarter, I'd say, is when AI felt interesting to completely profound and completely changing the way I personally approach work, the way LeanScale is a business approaches work. LeanScale, highly operationally intensive company. We're doing revenue operations for

## 32:44 — LeanScale's agent deployment; V1 to 95%

**[32:44]** VC-backed B2B startups. We have to move quickly. It's managing a multitude of systems and a wide breadth of services as well from marketing ops, sales ops, CS ops, and partnership ops. And what we've been able to do, and to be specific, we're leveraging everyone at LeanScale as a power user of cloud code. We've done a major deployment of OpenClaw. So every single person has their agents. We have purpose-built agents for our services as well. And we've been able to dramatically reduce the time it takes to deliver a project, deliver a service, and not just reduce time and make it more efficient, make it better. When you have access

**[33:30]** to a repo of the best knowledge in the world and then you have a meeting with someone, you feed it the transcript and it creates the project plan and pushes those to your PM server. That's not something that you can replicate in any other way. And like you were alluding to, we're just at the beginning. There's so much more that cloud code just released their own version of OpenClaw today as we record on March 24th, 2026. And every single week it feels like a whole new foundational addition and change here. I agree. And it takes effort to keep up with it all. It really does, but it's been a great

## 34:11 — AI as a self-coach: democratized training

**[34:11]** investment for myself and for our team for sure. I think this will only continue to be the case. I think one of the things though that maybe I'm not seeing too widely adopted potentially at this point, like everyone's using it for the basics of things, like particularly in a revenue organization, the next tier up from that or developing agent systems to solve for workflows or help basically autonomously support common workflows for reps or managers, et cetera. But using it for self-improvement and self-learning has been for me one of the things that I'm trying to lean into is sort of the next frontier, at least internally

**[35:03]** here where we don't have a huge sales enablement team. We don't have professional trainers coming in every couple of months or so. But with a little bit of effort, you can use these tools to self-analyze and self-critique in a completely safe, personalized environment and help improve your skillset in basically anything that you're doing or that's germane to the performance of your job. First, people need to be hungry for that input. They have to have a mindset of I want to get better at something. But hopefully you've solved that in the hiring process of figuring out who those folks are. But then to make it now

**[35:51]** this easy for folks to in the moment, even if their manager wasn't on a call with them or they're learning a new product, to get instant feedback or to think about how could I have fleshed out X better or asked this Y question better or something to that effect. How could I have said the explanation of that with 30% of the words? Any of those things is now instantly there for you. So it's beyond just executing on workflows or tasks, but to be thinking of it in terms of a training and improvement capacity I think is still an opportunity on the table for most. Can I share something? I think you'll find it interesting, probably funny. I have a agent

**[36:47]** purpose built to be my podcast coach. So every single episode is reviewed and I get a report card on quality of questions, cadence, talk time percentage, level of pushback and agreeability. And I think it's helped. It gave me suggestions that I would have never even thought about and there aren't a lot of podcast coaches on the market that I could have hired to help me do this. So a lot of that specialized training that also has the context of exactly what you're trying to do. It's not just generally speaking, I wholeheartedly agree. That's now become massively available to anyone. And I think whoever takes advantage of it is going

**[37:31]** to be an absolute weapon in the workforce. A hundred percent. The democratization of that type of training and coaching is massive and is not really being talked about much because in the old days you used to have to work for this big old company that had this really robust training program and you went away to sales school or had this formalized progression of training and whatnot, but that's gone, right? Now you can work for a two person company, a three person company, be completely young in your career and if you're willing to take advantage of these things, get just

**[38:16]** as good if not better of a training and educational experience for now your particular job in your particular application and company, which I think is really cool. Yeah, the specificity of it is completely unmatched compared to what alternatives have been up to date. I'm also thinking about I have three young kids, six, four and one and I obviously have some like existential AI questions as I'm guiding them through their stages. I'm like, I don't know if anything I did is going to be relevant. I do think one of the skills that's going to be absolutely crucial is critical thinking and I do worry

## 39:10 — Critical thinking, the mental gym, and education

**[39:10]** that heavy use of AI if not used intentionally is starting to degrade cognitive ability and I really do think that we're going to be at a place where you may have to go to a mental gym to make sure your brain is able to function and critically think and then use these tools in the right way or do things in manual mode on purpose just to train yourself. I completely agree because I mean, listen, the risk is you just start leaning on the AI to do everything and you take for granted its ability to do so in the right correct manner and I guess you could say the same thing about any traditional education, right?

**[40:04]** You can't just take for granted what you're being taught or what was said or it was even read, right? Sometimes like you need to have a critical thinking layer to everything and be willing to challenge ideas but I agree with you very much. That's a skill set that needs to be maintained for sure but the question is, yeah, is like your kids, I think you're just a bit older, my daughter's three and a half and so 15 years from now, you know, I honestly can't imagine she'll go to college, not in the way we know it today. Like that doesn't seem like it'll be a thing at that point, right? Like there'll be probably education

**[40:54]** but it'll probably be so focused on a very specific set of skills to do a particular job or to, you know, execute a particular function, right? Rather than this generalized kind of concept of a four-year degree, right? That's one of the shifts at least that is in my mind but at a base level, it won't be teaching like everyone like a surface layer of all the things which has been our approach to education for the last 60, 70, 80 years but be much more, we need to give people like you're talking about Anthony, like basic human skill sets around critical thinking, adaptability, resilience, like logic and other, you know,

**[41:49]** foundational skill sets that are not topic or subject specific and then allow people to have that base to use tools and get, you know, very, you know, sort of, you know, a deep siloed kind of education in one particular area based on whatever they want or need to do at that time. On the college topic because I think that's a spicy one, I think there's always going to be some way to differentiate status. I don't know if college will look exactly how it is today but there will be something expensive you can send your kids to. You can be sure of that. That will exist. I don't know exactly what they'll be learning

**[42:41]** you're doing but that 100% will exist because, you know, we have to keep the strata in order here or else maybe chaos can soothe but maybe and I think we'll experience significant mental atrophy if we don't address it and start doing things. I'm finding it myself. I have a tough time writing an email sometimes and like when did I forget how to write emails when I've been leaning on my AI agents to do everything for me and now I can't write a simple two sentence response like that's when I've had some of those moments it's making me think I've grown up doing this every single day and now I'm starting to have a tough time

**[43:26]** doing things in manual mode. How's a kid going to be able to handle that? Agree. I mean the other if we really I mean this is I mean this alone could have been an hour. Right. But if you have to then start to unpack and say all right but like do we really care that a kid can't write like they should have the ability to write and express their ideas through written language. Right. For sure. But like the things that we may lose I think are you know it's worth questioning are they really worth keeping like or should we be prioritizing their ability to do other things like or spend their time in a fundamentally different way. Right. If

**[44:11]** you know there's a lot of suggestion on well people may not need to work at some point. OK. Or at least you know a large swath of people may not need to work and you could work if you want to. But you may not need to. The answer to which of course is the only one answer I can think of is UBI universal basic income. And so in that in that world like let's say that that came to be then it's a question of well what should how should people be spending their time. What should they be doing. Right. That's satisfying. That's worthwhile. That gives them a sense of purpose and fulfillment. But you know if they can't

**[44:52]** send an email you know if they're not great at writing emails in that environment in that world. Do we care. I'm hoping it evolves into higher order activities and doesn't degrade into I just can't even do anything or think about things. But time will tell time will tell. I know it's it's it's a it's a tough topic a lot of people are wrestling with and I just think we're starting to get some interesting signals. But like there's that side and then there's also AI hasn't reduced work. People who are leveraging more are working even more. So once you realize there's tasks that you couldn't do before and now they're possible

## 45:37 — AI hasn't reduced work; achievement and the Harvard study

**[45:37]** now just more work gets put on your plate. So there's just some interesting things that are happening that I don't know if we were expecting as a society. Yeah that's that's an interesting one. I mean like my working hours certainly aren't less right. The amount that I'm able to accomplish and my output is certainly much higher. But I'm not working any less. But then again like I think you're going to have you know there's always going to be some types of folks that are just very driven to accomplish accomplish accomplish right to get stuff done. And you give them these kinds of tools that enable that and

**[46:18]** they keep getting that satisfaction of that beat that output. And you know Harvard did a big study many years ago on what makes people happy. The dominant the punchline of the study was it was achievement right. And it doesn't have to be big achievement can be micro achievements like even throughout the course of a day right. And so you give you play into that by AI being able to allow people to achieve slash produce things. People kind of will feed on that right. They're going to want to run right. They're going to run run with that and that's great right. But you know that that probably means that you know they do work more right or someone

**[47:01]** who is managing that kind of person and be like great like to handle do this too right. Keep going. If I can find a couple more of you to be 10 x productive you know more the merrier. Well I think I think one common thread that is going to be important for people who come out on top in this new era is just having that level of grit adaptability agility when the entire world is changing and the playbook you had before doesn't work anymore. There are people that can adapt to that well and then people who fall behind. And I think you have one of the most interesting experiences that sounds unbelievably challenging of starting

## 47:48 — Grit through crisis: the 2008 story and SVB

**[47:48]** a wealth management company right during the oh eight financial crisis. And I'll share with you my dad did work for Lehman Brothers. My mom was a she created a company doing loan officer recruitment for for banks. So I was coming up through high school right at the center of experiencing everything that was going on. And but you made it and you made it through. And I'm curious what was it that helped you adapt during that time and bring you to the new era. So yeah I mean my timing was impeccable. I had a few years. You know I graduated college and I didn't want to go start taking a I didn't want to go right into

**[48:41]** like a corporate type job. I wanted to see if I could do something for myself. So I started I started with this firm and started building out a team and then a practice and you know just managing money for folks. And we were cruising along building building. And then oh eight oh eight hit. And you know that was a job where you know it was it was my business it was an entrepreneurial. There was no there was no salary or anything like that. You know you either made money or you didn't. And so when that hit and I lost half of my business and the span of a couple of months basically it was pretty it was bad. And that just persisted

**[49:23]** for a bit. But it tell you you know that's the character building kind of pain right that helps you figure out that you know. I'm not going to give up on this. There's people that are depending on me and we're going to keep fighting and we're going to hang on and sort of you know build back again. And we did. And you know the years post oh wait we're some of our best ever. And you know for the folks that hung on we were able to shepherd them through that you know quite well. But that was like probably the first real big test for me in business. And in particularly you know that that experience and others and

**[50:09]** you know having to you know survive for yourself and just figure it out and persevere and in the face of tremendous adversity was something that I was able to carry forward through my startup experiences which are debatable whether they're more or less painful than the OA crisis. But you know the lessons were applicable because there's a lot of times and especially in early stage stuff where it's hard. It's just really really hard. It's a knife fight. You're going to feel like quitting and giving up from time to time and you just have to keep making the choice to keep going and keep fighting for it. And then figuring out ways to win as the

**[50:48]** circumstances change around you and the hand that you have to play even internally you know is constantly changing. And so that's where that adapt you know adaptability and resilience or in my opinion two most important characteristics for any business person. And so especially in startup stuff. Yeah my beginning wasn't as dramatic as the OA crisis but 2021 I started the back half of 21 and you know off the highest high of tech possible and then right into tech winter as I also banked with SVB and our entire payroll and capital got locked up there. So yeah I think expect the challenges take them as character building opportunities

**[51:39]** and just keep your eyes and ears open and be adaptable because I think it's going to happen whatever it is. There's going to be these peaks and valleys and when you're in there I think just hanging in and enduring has been the only thing that is for me. Just grit your teeth and keep going. That's right. That's all you can do. Just keep making the best decisions you possibly can. Work hard and yeah just don't give up. That's it. Never give up. And I think we're in places where like you mentioned we have a lot of people depending on us and giving up really isn't an option. Tom this was really really incredible.

## 52:21 — Closing: making work better

**[52:21]** Thank you so much for taking all of your experience that you've had and especially the mission of making work better, making it enjoyable. We're all spending so much time invested into our careers, our jobs, professional lives and that is worth pointing attention to and making it the best experience possible and from a business perspective when you do that as you mentioned there's plenty of data to show that it's going to show up in the results as well. You'll retain your employees. They'll be more productive and you'll show up better in the market and I love the stories that you shared about the grittiness of making

**[53:01]** it through it. I think if you can make it through that you could probably make it through anything and I'm just really excited to see what you do next. So thank you for being on the show and can't wait to keep up. Thank you so much Anthony. Very much enjoyed the conversation and love what you all are doing here at LeanScale and so all the best. Appreciate it.